title: Nucleophilic addition of potassium alkynyltrifluoroborates to D-glucal mediated by BF3 x OEt2: highly stereoselective synthesis of alpha-C-glycosides.
abstract: A convenient, mild and highly stereoselective method for C-glycosidation (alkynylation) of D-glucal with various potassium alkynyltrifluoroborates, mediated by BF3x OEt2 and involving oxonium intermediates, preferentially provides the alpha-acetylene glycoside products with good yields.
authors.affiliation: Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, Brazil.
authors.forename: Adriano S
authors.initials: AS
authors.lastname: Vieira
authors.forename: Pedro F
authors.initials: PF
authors.lastname: Fiorante
authors.forename: Thomas L S
authors.initials: TL
authors.lastname: Hough
authors.forename: Fernando P
authors.initials: FP
authors.lastname: Ferreira
authors.forename: Diogo S
authors.initials: DS
authors.lastname: Lüdtke
authors.forename: Hélio A
authors.initials: HA
authors.lastname: Stefani
mesh_terms: D001880:Boranes / Q000737:chemistry*; D001881:Borates / Q000737:chemistry*; D002125:Calcium Gluconate / Q000737:chemistry*; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D011188:Potassium / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D001880:Boranes; D001881:Borates; D006027:Glycosides; C021274:boron trifluoride; C098759:fluoroboric acid; D011188:Potassium; D002125:Calcium Gluconate